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A New Stereochemical Model from NMR for Benzoylated Cyclodextrins, Promising New Chiral Solvating Agents for the Chiral Analysis of 3,5-Dinitrophenyl Derivatives

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journal contribution
posted on 1997-02-21, 00:00 authored by Gloria Uccello-Barretta, Angela Cuzzola, Federica Balzano, Rita Menicagli, Anna Iuliano, Piero Salvadori
Hexakis(2,3-di-O-benzoyl)-α-cyclodextrin and hexakis(2,3,6-tri-O-benzoyl)-α-cyclodextrin have been employed as chiral solvating agents (CSAs) for the NMR determination of the enantiomeric composition of derivatives of chiral amines, amino alcohols, alcohols, carboxyl acids, and amino acids bearing a 3,5-dinitrophenyl moiety. The conformational features of the two cyclodextrins have been carefully analyzed by NMR spectroscopy, and the origin of the symmetry change (C6C3), detected by NMR for hexakis(2,3-di-O-benzoyl)-α-cyclodextrin in CDCl3, has been clarified.